(S)-(+)-(2-methylbutyryl)phloroglucinol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-(2-methylbutyryl)phloroglucinol
• 英文别名: 2-(2-methylbutyryl)phloroglucinol；multifidol；(S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one；1-(2,4,6-trihydroxyphenyl)-2-(S)-methylbutanone；2-methylbutanoyl phloroglucinol；(2S)-2-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: ASABIRFQGVWRDC-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-(2-methylbutyryl)phloroglucinol 在 咪唑 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.09h， 生成 (2S)-1-(2-(((2E)-3,7-dimethylocta-2,6-dien-1-yl)oxy)-4,6-dihydroxy-phenyl)-2-methylbutan-1-one
  参考文献：
  名称：

  酰基金葡糖醇的全合成及其对金黄色葡萄球菌多药耐药（MDR）和耐甲氧西林菌株的临床分离株的抗菌活性

  摘要：

  以生物测定为导向的药物发现工作着眼于金丝桃属的各种物种，导致发现了许多新的酰基间苯三酚，包括（S，E）-1-（2-（（3,7-dimethylocta-2,6-dien-来自H的1-基）氧基）-4,6-二羟基苯基）-2-甲基丁-1--1-酮（6，奥比汀A）。olympicum，与MIC值范围为0.5至1mg / L与一系列多药耐药（MDR）和耐甲氧西林的临床分离株的金黄色葡萄球菌（MRSA）菌株。奥林匹克霉素A的有前途的活性和有趣的化学反应促使我们进行6的全合成以及一系列类似物，以评估它们作为一组新的抗菌剂的结构活性特征。以下的合成6和结构上相关的acylphloroglucinols 7 - 15和18 - 24，其对一组抗细菌活性的金黄色葡萄球菌菌株进行评价。在间苯三酚核心上，由一个8至10个碳原子邻位至一个5个碳原子的酰基取代基组成的烷氧基的存在是重要的结构特征，有望实现抗葡萄球菌的活性。

  DOI：

  10.1016/j.ejmech.2018.05.038
• 作为产物：
  描述：

  (S)-(+)-2-甲基丁酸 在 aluminum (III) chloride 、 氯化亚砜 作用下， 以 二硫化碳 、 硝基苯 为溶剂， 反应 3.0h， 生成 (S)-(+)-(2-methylbutyryl)phloroglucinol
  参考文献：
  名称：

  酰基金葡糖醇的全合成及其对金黄色葡萄球菌多药耐药（MDR）和耐甲氧西林菌株的临床分离株的抗菌活性

  摘要：

  以生物测定为导向的药物发现工作着眼于金丝桃属的各种物种，导致发现了许多新的酰基间苯三酚，包括（S，E）-1-（2-（（3,7-dimethylocta-2,6-dien-来自H的1-基）氧基）-4,6-二羟基苯基）-2-甲基丁-1--1-酮（6，奥比汀A）。olympicum，与MIC值范围为0.5至1mg / L与一系列多药耐药（MDR）和耐甲氧西林的临床分离株的金黄色葡萄球菌（MRSA）菌株。奥林匹克霉素A的有前途的活性和有趣的化学反应促使我们进行6的全合成以及一系列类似物，以评估它们作为一组新的抗菌剂的结构活性特征。以下的合成6和结构上相关的acylphloroglucinols 7 - 15和18 - 24，其对一组抗细菌活性的金黄色葡萄球菌菌株进行评价。在间苯三酚核心上，由一个8至10个碳原子邻位至一个5个碳原子的酰基取代基组成的烷氧基的存在是重要的结构特征，有望实现抗葡萄球菌的活性。

  DOI：

  10.1016/j.ejmech.2018.05.038

文献信息

• Anti-Bacterial Agents
  申请人：Gibbons Simon

  公开号：US20100222426A1

  公开（公告）日：2010-09-02

  The invention relates to novel acylphloroglucinols which have strong growth inhibitory effects on multi-drug resistant strains of bacteria, particularly MRSA. Typically the compounds have a terpene substituent, or a terpene-derived substituent. Methods of isolating the compounds from natural sources, and synthetic methods for forming the compounds are also provided.

  这项发明涉及新型酰基苯酚萜类化合物，对多药耐药菌株，尤其是MRSA具有强烈的生长抑制作用。通常这些化合物具有萜类取代基或萜类衍生取代基。同时还提供了从天然来源分离这些化合物的方法，以及合成这些化合物的方法。
• Biomimetic Total Synthesis of Hyperjapones A–E and Hyperjaponols A and C
  作者：Hiu C. Lam、Justin T. J. Spence、Jonathan H. George

  DOI：10.1002/anie.201606091

  日期：2016.8.22

  natural products of mixed aromatic polyketide and terpene biosynthetic origin that have recently been isolated from Hypericum japonicum. We have synthesized hyperjapones A–E using a biomimetic, oxidative hetero‐Diels–Alder reaction to couple together dearomatized acylphloroglucinol and cyclic terpene natural products. Hyperjapone A is proposed to be the biosynthetic precursor of hyperjaponol C through a sequence

  Hyperjapones A–E和Hyperjaponols A–C是混合芳香族聚酮化合物和萜烯生物合成来源的复杂天然产物，最近从日本贯叶连翘中分离出来。我们使用仿生的氧化杂Diels-Alder反应合成了脱脂甲醚A–E，将脱芳香化的酰基间苯三酚和环状萜烯天然产物偶联在一起。通过以下一系列步骤，提出了高japeone A是高japonol C的生物合成前体：1）环氧化； 2）环氧化。2）酸催化的环氧化物开环；3）一致的异步烯烃环化和叔碳正离子的1,2-烷基转移。拟议中的生物合成过程的化学模拟使得高japonol C的简明全合成得以完成，其中仅需四个步骤即可构建六个碳-碳键，六个立体中心和三个环。
• Crombie, Leslie; Jones, Raymond C. F.; Palmer, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 353 - 358
  作者：Crombie, Leslie、Jones, Raymond C. F.、Palmer, Christopher J.、Begley, Michael J.

  DOI：——

  日期：——
• Tricyclic Acylphloroglucinols from <i>Hypericum lanceolatum</i> and Regioselective Synthesis of Selancins A and B
  作者：Serge A. T. Fobofou、Katrin Franke、Andrea Porzel、Wolfgang Brandt、Ludger A. Wessjohann

  DOI：10.1021/acs.jnatprod.5b00673

  日期：2016.4.22

  The chemical investigation of the chloroform extract of Hypericum lanceolatum guided by H-1 NMR, ESIMS, and TLC profiles led to the isolation of 11 new tricyclic acylphloroglucinol derivatives, named selancins A-I (1-9) and hyperselancins A and B (10 and 11), along with the known compound 3-O-geranylemodin (12), which is described for a Hypericum species for the first time. Compounds 8 and 9 are the first examples of natural products with a 6-aryl-2,2-dimethylchroman-4-one core fused with a dimethylpyran unit. The new compounds 1-9 are rare acylphloroglucinol derivatives with two fused dimethylpyran units. Compounds 10 and 11 are derivatives of polycyclic polyprenylated acylphloroglucinols related to hyperforin, the active component of St. John's wort. Their structures were elucidated by UV, IR, extensive 1D and 2D NMR experiments, HRESIMS, and comparison with the literature data. The absolute configurations of 5, 8, 10, and 11 were determined by comparing experimental and calculated electronic circular dichroism spectra. Compounds 1 and 2 were synthesized regioselectively in two steps. The cytotoxicity of the crude extract (88% growth inhibition at 50 mu g/mL) and of compounds 1-6, 8, 9, and 12 (no significant growth inhibition up to a concentration of 10 mM) against colon (HT-29) and prostate (PC-3) cancer cell lines was determined. No anthelmintic activity was observed for the crude extract.
• Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives
  作者：Li Feng、Marcus M. Maddox、Md. Zahidul Alam、Lissa S. Tsutsumi、Gagandeep Narula、David F. Bruhn、Xiaoqian Wu、Shayna Sandhaus、Robin B. Lee、Charles J. Simmons、Yuk-Ching Tse-Dinh、Julian G. Hurdle、Richard E. Lee、Dianqing Sun

  DOI：10.1021/jm500853v

  日期：2014.10.23

  On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 mu g/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2',4'-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.